Sunsets and Sailing in Santorini

Santorini is beautiful – stunning sunsets, incredible views from nearly everywhere on the island. It’s crowded with tourists, mostly of the honeymooning variety. Couples everywhere (that’s a warning). Our group of five women stood out among all of the romance and we loved it. The other type of tourists are young partying backpackers, likely of the Australian variety. Watch out for them too.

You will only need a couple nights in Santorini. Don’t be fooled by its beauty – it’s small and there really isn’t that much to do. After a few days you will be sick of the crowds and ready for a new island.

those caldera views

Getting There: We flew from Athens to Santorini, about 45 minutes. It is also possible to take a ferry from neighboring islands into Santorini (we took the ferry when we left the island en route to Crete).

Where to Stay: We stayed in Fira at Anatoli Hotel . Close to center of town, but not super expensive. Didn’t have caldera views and not fancy (like most of the other hotels we saw in Santorini). But it was perfect for what we needed and easy to get around Fira town from there. Free wifi, but only in common areas of the hotel. Maria and Evaggelia (owner) were so nice and very helpful. They helped us arrange rental cars, gave us directions, made reservations for dinner for us (they always seemed to think that was unnecessary, but we’re New Yorkers and like to make plans especially when there are so many honeymooning couples everywhere). Pool area was very nice, breakfast included and was very good: yogurt, cereal, bread, cheese, some baked item like a cheese pie or omelet.

We rented a car 2 days in Santorini (for wineries and to explore beaches), cost 55 euro for the day and company dropped off and picked up for us at our hotel. Easy to get around the island with a car, though the narrow roads can be a little frightening as they are nearly on a cliff. It’s helpful to have the rental car to get around to other parts of the island when you are not just sticking around the towns.

Eating & Drinking in Santorini:

As mentioned above, you might not need reservations for all places, but it can’t hurt to call ahead, especially for restaurants overlooking the caldera. Most restaurants get very crowded and you will likely have to wait a bit for a table.

Kyrpida – Didn’t have a great view, but we couldn’t get in anywhere else. While the view wasn’t great, it was a nice place and we got some shade. We ordered Mythos (no wine), fava, Greek salad, green salad with figs, meatballs (so good), roasted mushrooms (awesome), sea bream (really good and not too large) and tzatziki.

Franco’s – Come here for a drink at sunset. Fantastic views of the caldera and relatively empty so you wont have to deal with the crazy crowds. Drinks are expensive here and music was a little loud, but overall nice place to watch the sunset.

Naoussa – Came here for dinner after drinks and sunset at Franco’s. We were told we could sit outside, but that didn’t happen. We did at least sit at a table closest to the water. Food was really good though, definitely one of our favorite meals. We ordered tzatziki with pita bread, tomato balls (these are a Santorini specialty but not really our thing, like a fried covering around a bit of tomato paste), fava, bread, sardines, roasted mushrooms (one of our least favorite dishes), and baklava. This was our first baklava in Greece and a bit disappointing as it tasted mostly like carrot cake.

Kira Thira – Jazz bar in Santorini (apparently also the oldest). Looked really cool from the outside and like a low key place to grab a few drinks. Super disappointing – the drinks were awful. My aperol spritz tasted like cough medicine. We asked for new drinks, but they wouldn’t take our old drinks back and treated us like we were ignorant of how the drink was made. Everyone else said their drinks were awful too so would advise to get only bottled drinks that they can’t screw up.

Town Club/Highlander – Dance clubs/bars where we felt really old. But the music was good for dancing.

Ammoudi Bay – This is located in Oia, but down near the water. There are a string of restaurants, all very similar, and you basically walk through each one to get to the next. All of the restaurants serve fresh fish. There are octopi drying out along the water so you know this will be good! Way less crowded than dinner in Oia and Fira. Drive and park as close as you can to the port and watch the sunset there before dinner. We chose to go to Katina which wasn’t very crowded. Service was so so – lots of up sell on the fish, claiming we needed to get the giant grouper to feed all of us (120 euro) but we knew that was too much. Ordered a sea bream instead which was a third of the price. Also ordered fava, saganaki, octopus (also fresh), and baklava. We sat right in front of the grill so saw all of the fresh fish being cooked.

Idol Restaurant – Another restaurant with a caldera view. We went during lunch time instead of at night. Food was pretty good, had codfish loudamakes in a beet sauce (amazing), fava which came on toast with anchovies, a salad with tomatoes croutons and goat cheese, and roasted mushrooms. All really good. Pretty empty at lunch.

Things to Do:

Fira and Oia, the two main towns in Santorini, have lots of shops, snack places (gelato), and bars. And lots of tourists.

Oia – These are the postcard views you’ve seen with the white buildings and sunsets. As such, there are lots of tourists around, especially at sunset. Parking available (free, but few spaces available)

Wineries – Not recommended. We decided to do wineries, but on our own and not through a tour since we had rental car. First we visited Santo which had awesome views, but was very commercial/touristy. We did the 6 tasting with cheese plate. We ordered 4 of these (for 5 people) and was way too much cheese. Would suggest ordering the tastings and one cheese plate to share. Didn’t love the wines, some of the whites were nice but the reds were too sweet. I liked the vinsanto, though no one else did. We then drove up to Oia to Domaine Sigalas winery. Much cuter and smaller, but not great views. We only tried 3 wines each (4 people cost 6.30 euro) and had a plate of bread and oil. Whites were good, did not care for the rose.

Catamaran Cruise – We took a cruise with Santorini Sailing. This was a highlight of our trip. We did the semi private tour (150 euro) which was our group of 5 plus three couples. Price included a half day of sailing with some swimming around the Red Beach and the caldera, lunch, and drinks. Lunch was great – calamari, chicken, pork, pasta, salad, prawns. They are also accommodating for vegetarians or food allergies. We were so happy we did this tour – if we could have afforded to do it again, we would have done it the next day. Got to see the warm springs in the caldera (don’t wear a light colored swim suit as it could turn orange) and get a great view of the entire island. The tour was over by about 2/2:30.

Beaches – Recommend renting a car to get to the beach club. We drove down to Polivares where there are a bunch of clubs. We went to Jojo as we heard it was good/fun place and they also had a pool there in case we wanted to switch it up from the beach. Free hut rental, though with five people we got one janky chair. Massages available on the beach, great service from our flirty waiter Fotis (we loved the call button at our chairs). The beaches in Santorini are black sand and thus very hot and rocky. Good music all day and food was great. We could have stayed there all day and night.